Advances in the Chemistry of Tetrahydroquinolines

Abstract

Involving the Generation of Two Bonds 5.1. Introduction 5.2. Formation of the NÀC 2 and C 3 ÀC 4 Bonds 5.2.1. DielsÀAlder Related Reactions 5.2.2. Tandem Michael AdditionÀCyclization Sequence 5.2.3. Miscellaneous Reactions 5.3. Formation of the NÀC 2 and C 4 ÀC 4a Bonds 5.3.1. Michael Addition Initiated Reactions 5.3.2. Miscellaneous Reactions 5.4. Formation of the NÀC 2 and C 2 ÀC 3 Bonds 5.5. Formation of the C 2 ÀC 3 and C 3 ÀC 4 Bonds 5.6. Formation of the C 2 ÀC 3 and C 4 ÀC 4a Bonds 5.7. Formation of the C 3 ÀC 4 and C 4 ÀC 4a Bonds 5.8. Formation of the C 8a ÀN and C 4 ÀC 4a Bonds 5.9. Formation of the NÀC 2 and C 8a ÀN Bonds 6. Synthesis of 1,2,3,4-Tetrahydroquinolines Involving the Generation of Three or More Bonds 6.1. Formation of the NÀC 2 , C 2 ÀC 3 , and C 4 ÀC 4a Bonds: The Povarov and Related Reactions

Grinding and Milling: Two Efficient Methodologies in the Solvent-Free Phosphomolybdic Acid-Catalyzed and Mechanochemical Synthesis ofcis-4-Amido-N-yl-2-methyl-tetrahydroquinolines

“…12, 2016 Their rapid construction can be easily achieved via imino DA reaction (Povarov reaction), using a great variety of commercial anilines, aldehydes and electron-rich alkenes (dienophile). [9][10][11] Recently, the scientific interest on the acid-catalyzed three component ABB' Povarov reaction has increased due to the possibility to generate, in a domino process, structurally differentiated and privileged 2,4-disubstituted THQs with pharmaceutical and new materials applications. [12][13][14] However, there are still main drawbacks in the 2-Me-THQ synthesis via ABB' reactions: expensive reagents including additives and catalysts, toxic and dangerous solvents, and energetic demand (reaction parameters reach until 200 °C).…”

Aluminum triflate catalyzed Povarov reaction for the synthesis of pyranotetrahydroquinolines

“…[1][2][3][4][5] Owing to their importance, a number of synthetic strategies have been developed for their synthesis. 1,[6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] The reaction of an aromatic imine (in a two component reaction) or aniline (in a three component reaction) with benzaldehyde and electron rich dihydropyran (DHP) in the presence of an acid catalyst/promotor, known as the Povarov reaction, 1,[19][20][21][22][23][24] has been the common and convenient synthetic protocol for the preparation of such important compounds. Several acid catalysts/promoters, which include the following, have been reported in the literature: InCl 3 , 9 Sc(OTf) 3 32 Tritylium Cation, 33 and phosphoric acid.…”

Synthesis and in vitro evaluation of 4-substituted furano[3,2-c] tetrahydroquinolines as potential anti-cancer agents

“…Meanwhile we plan to incorporate these two moieties to explore, it is a remarkable fact that the substituted furano [3,2-c] tetrahydroquinoline moiety, as an important scaffold that has potential antitumor biological activities ( Figure 1). Due to their structural novelty and important biological activities, the synthesis of complex chiral molecules around a biologically relevant framework has played an important role in the discovery of drugs 14 . Furthermore, some 2-phenylbenzofuran analogues have showed potent anticancer activities [15][16][17] .…”